Owner Dan Gilbert has offered Chauncey Billups a five-year contract to head up the Cavaliers front office, but Billups has yet to accept, sources with knowledge of the talks told The Athletic.

The two spent all day Wednesday at Quicken Loans Arena, where Billups was introduced to a number of the executives who would be working under him, one source with knowledge of the meeting told The Athletic. It was the second consecutive day of meetings between Gilbert and Billups.

If he accepts, the 40-year-old Billups will oversee operations despite having no prior front office experience. But he was a five-time All-Star, won a championship and was named a Finals MVP during his 17-year career. He has played alongside Carmelo Anthony in Denver and New York and Chris Paul in Los Angeles — two of LeBron James' closest friends. Billups is also close friends with Cavs coach Tyronn Lue.

Billups most recently served as an ESPN analyst. He isn't the first to step out of the television booth and into an executive's chair. Before he was head coach of the Golden State Warriors, Steve Kerr was a former player who left television to run the Suns. David Griffin worked under him in Phoenix.

Billups and the revamped front office are facing a difficult task of trying to close the gap on the Golden State Warriors and upgrade the roster with few trade assets. Former Cavs general manager David Griffin was talking to the Indiana Pacers about a trade involving Kevin Love and Paul George before the team announced Monday night he would not return as GM. Griffin traded away seven first-round picks to build the Cavs into champions. The only remaining trade chips are Love and a 2021 first-round pick.

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Jason Lloyd is the NBA Lead for The Athletic covering the Cavaliers. Jason previously spent seven years covering the Cavs for the Akron Beacon Journal. His first book, "The Blueprint: LeBron James, Cleveland's Deliverance and the Making of the Modern NBA" is due out this fall. Follow Jason on Twitter @JasonLloydNBA. If you liked this story, subscribe today for access to all of our ad-free content. Plans start at just $4.99 per month.